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Merck

638072

Sigma-Aldrich

SPhos

greener alternative

98%

Sinónimos:

SPhos, 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos

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About This Item

Fórmula empírica (notación de Hill):
C26H35O2P
Número de CAS:
Peso molecular:
410.53
Número MDL:
Código UNSPSC:
12352128
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

Ensayo

98%

idoneidad de la reacción

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: Heck Reaction

reagent type: ligand
reaction type: Kumada Coupling

reagent type: ligand
reaction type: Negishi Coupling

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

puntuación de productos alternativos más sostenibles

old score: 10
new score: 1
Find out more about DOZN™ Scoring

características de los productos alternativos más sostenibles

Waste Prevention
Less Hazardous Chemical Syntheses
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

164-166 °C (lit.)

grupo funcional

phosphine

categoría alternativa más sostenible

cadena SMILES

COc1cccc(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4

InChI

1S/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3

Clave InChI

VNFWTIYUKDMAOP-UHFFFAOYSA-N

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Descripción general

SPhos [2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Less Hazardous Chemical Syntheses” and “Inherently Safer Chemistry for Accident Prevention”. Click here to view its DOZN scorecard.

Aplicación

Learn more about Buchwald Phosphine Ligands

For small scale and high throughput uses, product is also available as ChemBeads (932191)
Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.
SPhos may be used as a ligand in the following processes:
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.
  • Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.
Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation.

Información legal

Usage subject to Patents: US 6307087; EP 1097158; JP 5758844; CA 2336691

Producto relacionado

Referencia del producto
Descripción
Precios

Código de clase de almacenamiento

13 - Non Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Evidence for the formation and structure of palladacycles during Pd-catalyzed C-N bond formation with catalysts derived from bulky monophosphinobiaryl ligands.
Eric R Strieter et al.
Angewandte Chemie (International ed. in English), 45(6), 925-928 (2005-12-29)
Synthesis and Suzuki-Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides.
Molander GA and Shin I.
Organic Letters, 13(15), 3956-3959 (2011)
Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXR? agonists
Hioki, Hideaki, et al.
Bioorganic & Medicinal Chemistry Letters, 19.3, 738-741 (2009)
Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRa agonists.
Hioki H, et al.
Bioorganic & Medicinal Chemistry Letters, 19(3), 738-741 (2009)
Pd-catalyzed Kumada-Corriu cross-coupling reactions at low temperatures allow the use of Knochel-type Grignard reagents.
Ruben Martin et al.
Journal of the American Chemical Society, 129(13), 3844-3845 (2007-03-14)

Artículos

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

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Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

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